You can cut the stem down a little. It can be uncomfortable if the stem is too long, but I would never cut the stem off because it helps me find the bottom of the cup each time.

As far as putting it in- i do the method where you hold the cup sideways and push down on the top of it ( around the rim of the cup) and then try to squish it at small as I can like a little taco. Lol Hope that makes sense. While putting the cup in... Hold it tight together and go straight back and then up. ( makes sure you do this while still holding it tight like a taco) orherwise the cup may pop open prematuraly when its not all the way in. I do twist it a little as best I can until it feels the most comfortable and in there. I do get leaks sometimes, but ever since having 2 children I would get leaks with tampons too. I wear cloth pantyliners with my Ladycup.